1-(2-Imidazol-1-yl-ethyl)-piperazine → 6-Methoxyquinoline-3-carbonitrile

HRID 499121노트

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HRID 499121 반응식
ClC1C=C(N[C:16]2[C:25]3[C:20](=[CH:21][C:22](F)=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]=[CH:18][C:17]=2[C:29]#[N:30])C=CC=1SC1N(C)C=CN=1.N1(CCN2CCNCC2)C=CN=C1>CN1CCCC1=O>[CH3:27][O:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][C:17]([C:29]#[N:30])=[CH:16]2

참가 물질

4

반응물 2

HCID 27593491-(2-Imidazol-1-yl-ethyl)-piperazineHCID 234980744-[3-chloro-4-(1-methyl-1H-imidazole-2-ylsulfanyl)phenylamino]-7-fluoro-6-methoxyquinoline-3-carbonitrile

생성물 1

HCID 198561466-Methoxyquinoline-3-carbonitrile

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
105 °C

실험 절차

Following the procedure of Example 11, a mixture of 220 mg (0.5 mmol) of 4-[3-chloro-4-(1-methyl-1H-imidazole-2-ylsulfanyl)-phenylamino]-7-fluoro-6-methoxyquinoline-3-carbonitrile and 290 mg (1.6 mmol) of 1-(2-imidazole-1-yl-ethyl)piperazine in 1.2 mL of 1-methyl 2-pyrrolidinone is heated at 105° C. for 20 hours to yield the crude product. Purification by silica gel chromatography (gradient 95:5-methylene chloride/methanol to 85:15 methylene chloride/methanol) gives 210 mg of 4-({3-chloro-4-[(1-methyl-1H-imidazole-2-yl)thio]phenyl}amino)-7-{4-[2-1H-imidazole-1-yl)ethyl]piperazin-1-yl}-6-methoxyquinoline-3-carbonitrile as a beige solid, mp 251-253° C.

후처리

  1. customto yield the crude product
  2. customPurification by silica gel chromatography (gradient 95:5-methylene chloride/methanol to 85:15 methylene chloride/methanol)

출처 및 근거

ORD 기록
ord-8b21cf1ed9bd4fceb2bfaefbf77ef585
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767671B2

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